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The title compound, C12H24O3, was prepared by the RuO4-catalyzed oxidative cyclization of 2,9-dimethyl­deca-2,8-diene. The crystal structure determination has shown unambigously that ring closure produced the trans stereoisomer. Intra­molecular O—H...O hydrogen bonding generates an S(8) ring motif. Inter­molecular O—H...O hydrogen bonding leads to the formation of infinite C22(4) chains running along the a axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807022428/hb2377sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807022428/hb2377Isup2.hkl
Contains datablock I

CCDC reference: 651442

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.044
  • wR factor = 0.102
  • Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C2 = ... R PLAT793_ALERT_1_G Check the Absolute Configuration of C7 = ... R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Ruthenium tetroxide is able to catalyze the stereoselective synthesis of 2,5-bishydroxyalkyl-substituted THF and/or THP rings from 1,5- and 1,6-dienes, respectively, via oxygen transfer to the diene system, in the presence of sodium periodate as reoxidant (Charlsen et al., 1981; Piccialli, 2000; Piccialli & Cavallo, 2001; Albarella et al., 2001; Roth et al., 2005; Roth & Stark, 2006). Related oxidative cyclization processes, mediated by other transition metal-oxo species such as OsO4, MnO4-, RuO4-, are also known (Brown & Keily, 2001; de Champdoré et al., 1998; Piccialli & Caserta, 2004; Donohoe & Butterworth, 2003). We decided to investigate the same oxidative transformation on 1,7-dienes envisaging that the process could lead to the formation of oxepane rings as well.

Seven-membered oxacycles are present in many biologically active natural products such as Laurencia acetogenin metabolites and ether marine toxin. In these compounds the oxepane ring is very often 2,7 dialkylsubstituted. While some efficient methods toward the stereoselective synthesis of 2,7-cis-oxepanes have been developed, few methods have been so far devised to generate the 2,7-trans-oxepane system (Hoberg, 1998; Matsumura et al., 2000). Thus, taking into account the electrophilic character of RuO4, and precedents from the oxidation of 1,5- and 1,6-dienes, 2,9-dimethyldeca-2,8-diene was initially selected as a good substrate to test this possibility.

In this paper we report that the ruthenium-catalyzed oxidative cyclization of 2,9-dimethyldeca-2,8-diene gives the trans-oxepane diol product, (I). The X-ray analysis showed that the (R,R), (S,S) racemic mixture is formed, with the molecule in trans-configuration (Fig. 1 and Table 1). The oxepane ring adopts a twisted-chair conformation (Table 1) as usually found in oxepane derivatives (Luger et al., 1991). This conformation appears also to be the one adopted by mono-p-bromobenzoate derivative of (I) in solution as indicated by NOE data and J values.

This is the first report dealing with the synthesis of an oxepane product through oxidative cyclization of an 1,7-diene.

Crystal packing with indication of H bonds is shown in Fig. 2. Hydrogen bonds are summarized in Table 2. There is an intramolecular hydrogen bond, whose graph set descriptor is S(8), from O3 donor to O2 acceptor, leading to the formation of an eight-membered ring.

Molecules in the crystals are linked through intermolecular O—H···O bonds forming chains running along a, whose graph set descriptor is C22(4). The rows are generated by the glide planes normal to c axis.

Related literature top

For related literature, see: Albarella et al. (2001); Brown & Keily (2001); de Champdoré et al. (1998); Charlsen et al. (1981); Donohoe & Butterworth (2003); Luger et al. (1991); Matsumura et al. (2000); Piccialli (2000); Piccialli & Cavallo (2001); Roth & Stark (2006); Roth et al. (2005).

For related literature, see: Hoberg (1988); Piccialli & Caserta (2004).

Experimental top

The oxidative cyclization was accomplished as shown in Scheme 1. Ru-catalyzed oxidative cyclizations of dienes are generally conducted in solvent mixtures containing water (e.g EtOAc/CH3CN/H2O, 3:3:1) to dissolve NaIO4 that acts as the final oxidant. However, exclusion of water from the reaction mixture has recently been demonstrated to increase the yields of the THF diols obtained from the oxidation of 1,5-dienes. (Roth et al., 2005). Therefore, after some experimentation, the process was run in EtOAc/CH3CN (1:1) with NaIO4 (7 equiv.) supported on wet silica. These conditions proved very effective giving trans-oxepane (I) in an isolated 63% yield (HPLC, hexane/EtOAc, 7:3, Rt= 34 min) with >95% stereoselectivity level.

In particular, to a suspension of NaIO4 supported on wet silica (7 eqiv, 1.90 g) in EtOAc/CH3CN (1:1, 5.8 ml) was added 2,9-dimethyldeca-2,8-diene in EtOAc/CH3CN (1:1, 0.5 ml). Then, RuCl3 (160 µL of a 0.1 M stock solution in EtOAc, 5 mol %) was added via syringe, at 273 K under stirring. After 15 min reaction, TLC analysis (I2) showed complete consumption of the diene and formation of a product at Rf 0.6 (EtOAc/hexane, 7:3). The process was quenched by addition of a few drops of isopropylalcohol. The mixture was filtered and the solid washed with EtOAc and MeOH and the crude mixture chromatographed over a Si-gel column (25 × 0.5 cm). Elution with EtOAc-petroleum ether (1:1, 50 ml) gave 20 mg (63%) of the pure oxepane diol (I).

1H-NMR (500 MHz, CDCl3): δ 3.63 (1H, dd, J=10.6, 2.2, H-3/H-8), 1.94, 1.87 (2H each, H2-4/H2-7), 1.52, 1.37 (2H each, H2-5/H2-6), 1.22, 1.16 (6H each, 4 x Me). 13C NMR (75 MHz, CDCl3) δ 82.6, 73.9, 29.6, 27.8, 27.7, 24.2.

Single crystals of (I) suitable for structure determination were obtained from a chloroform solution by slow evaporation at room temperature.

Refinement top

The H atoms were located in difference maps and their coordinates were refined with Uiso(H) = Ueq(carrier).

Structure description top

Ruthenium tetroxide is able to catalyze the stereoselective synthesis of 2,5-bishydroxyalkyl-substituted THF and/or THP rings from 1,5- and 1,6-dienes, respectively, via oxygen transfer to the diene system, in the presence of sodium periodate as reoxidant (Charlsen et al., 1981; Piccialli, 2000; Piccialli & Cavallo, 2001; Albarella et al., 2001; Roth et al., 2005; Roth & Stark, 2006). Related oxidative cyclization processes, mediated by other transition metal-oxo species such as OsO4, MnO4-, RuO4-, are also known (Brown & Keily, 2001; de Champdoré et al., 1998; Piccialli & Caserta, 2004; Donohoe & Butterworth, 2003). We decided to investigate the same oxidative transformation on 1,7-dienes envisaging that the process could lead to the formation of oxepane rings as well.

Seven-membered oxacycles are present in many biologically active natural products such as Laurencia acetogenin metabolites and ether marine toxin. In these compounds the oxepane ring is very often 2,7 dialkylsubstituted. While some efficient methods toward the stereoselective synthesis of 2,7-cis-oxepanes have been developed, few methods have been so far devised to generate the 2,7-trans-oxepane system (Hoberg, 1998; Matsumura et al., 2000). Thus, taking into account the electrophilic character of RuO4, and precedents from the oxidation of 1,5- and 1,6-dienes, 2,9-dimethyldeca-2,8-diene was initially selected as a good substrate to test this possibility.

In this paper we report that the ruthenium-catalyzed oxidative cyclization of 2,9-dimethyldeca-2,8-diene gives the trans-oxepane diol product, (I). The X-ray analysis showed that the (R,R), (S,S) racemic mixture is formed, with the molecule in trans-configuration (Fig. 1 and Table 1). The oxepane ring adopts a twisted-chair conformation (Table 1) as usually found in oxepane derivatives (Luger et al., 1991). This conformation appears also to be the one adopted by mono-p-bromobenzoate derivative of (I) in solution as indicated by NOE data and J values.

This is the first report dealing with the synthesis of an oxepane product through oxidative cyclization of an 1,7-diene.

Crystal packing with indication of H bonds is shown in Fig. 2. Hydrogen bonds are summarized in Table 2. There is an intramolecular hydrogen bond, whose graph set descriptor is S(8), from O3 donor to O2 acceptor, leading to the formation of an eight-membered ring.

Molecules in the crystals are linked through intermolecular O—H···O bonds forming chains running along a, whose graph set descriptor is C22(4). The rows are generated by the glide planes normal to c axis.

For related literature, see: Albarella et al. (2001); Brown & Keily (2001); de Champdoré et al. (1998); Charlsen et al. (1981); Donohoe & Butterworth (2003); Luger et al. (1991); Matsumura et al. (2000); Piccialli (2000); Piccialli & Cavallo (2001); Roth & Stark (2006); Roth et al. (2005).

For related literature, see: Hoberg (1988); Piccialli & Caserta (2004).

Computing details top

Data collection: COLLECT (Nonius, 1999); cell refinement: DIRAX/LSQ (Duisenberg et al., 2000); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. View of the (R,R) enantiomer of (I). Displacement ellipsoids are drawn at 30% probability level (arbitrary spheres for the H atoms).
[Figure 2] Fig. 2. Partial crystal packing of (I) showing H bonding patterns as dashed lines.
[Figure 3] Fig. 3. The reaction scheme for the formation of (I).
rac-2,7-bis(2-hydroxy-2-propyl)-trans-oxepane top
Crystal data top
C12H24O3F(000) = 960
Mr = 216.31Dx = 1.119 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 86 reflections
a = 8.4400 (16) Åθ = 3.4–19.5°
b = 16.473 (3) ŵ = 0.08 mm1
c = 18.470 (5) ÅT = 173 K
V = 2567.9 (10) Å3Prism, colourless
Z = 80.25 × 0.20 × 0.10 mm
Data collection top
Bruker-Nonius KappaCCD
diffractometer
2926 independent reflections
Radiation source: fine-focus sealed tube1811 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.082
Detector resolution: 9 pixels mm-1θmax = 27.5°, θmin = 3.3°
CCD rotation images, thick slices scansh = 1010
Absorption correction: multi-scan
(SADABS; Bruker–Nonius, 2002)
k = 1721
Tmin = 0.978, Tmax = 0.988l = 2321
20554 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: difference Fourier map
wR(F2) = 0.102Only H-atom coordinates refined
S = 1.02 w = 1/[σ2(Fo2) + (0.038P)2 + 0.5591P]
where P = (Fo2 + 2Fc2)/3
2926 reflections(Δ/σ)max < 0.001
208 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.17 e Å3
Crystal data top
C12H24O3V = 2567.9 (10) Å3
Mr = 216.31Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 8.4400 (16) ŵ = 0.08 mm1
b = 16.473 (3) ÅT = 173 K
c = 18.470 (5) Å0.25 × 0.20 × 0.10 mm
Data collection top
Bruker-Nonius KappaCCD
diffractometer
2926 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker–Nonius, 2002)
1811 reflections with I > 2σ(I)
Tmin = 0.978, Tmax = 0.988Rint = 0.082
20554 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.102Only H-atom coordinates refined
S = 1.02Δρmax = 0.24 e Å3
2926 reflectionsΔρmin = 0.17 e Å3
208 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.00809 (12)0.04118 (6)0.90900 (5)0.0255 (3)
O20.10634 (13)0.07424 (7)0.77014 (6)0.0345 (3)
H2O0.185 (2)0.0479 (11)0.7584 (9)0.035*
O30.15740 (14)0.01681 (7)0.78139 (5)0.0312 (3)
H3O0.072 (2)0.0072 (11)0.7781 (8)0.031*
C20.15237 (18)0.00501 (9)0.91339 (8)0.0270 (4)
H20.1361 (17)0.0388 (10)0.9560 (8)0.027*
C30.2978 (2)0.04707 (11)0.92827 (9)0.0323 (4)
H3A0.3339 (18)0.0754 (10)0.8836 (9)0.032*
H3B0.382 (2)0.0112 (10)0.9424 (9)0.032*
C40.2726 (2)0.10787 (11)0.98981 (9)0.0379 (4)
H4A0.207 (2)0.0818 (10)1.0290 (8)0.038*
H4B0.377 (2)0.1205 (10)1.0105 (9)0.038*
C50.1973 (2)0.18820 (11)0.96685 (10)0.0385 (4)
H5A0.265 (2)0.2133 (10)0.9287 (9)0.039*
H5B0.199 (2)0.2266 (10)1.0091 (9)0.039*
C60.0286 (2)0.18288 (10)0.93785 (9)0.0320 (4)
H6A0.0038 (19)0.2358 (10)0.9216 (8)0.032*
H6B0.044 (2)0.1686 (9)0.9770 (8)0.032*
C70.01118 (18)0.12087 (9)0.87740 (8)0.0253 (3)
H70.1026 (19)0.1262 (9)0.8431 (8)0.025*
C80.13765 (18)0.12793 (10)0.82998 (8)0.0291 (4)
C90.2878 (2)0.10296 (12)0.86928 (10)0.0355 (4)
H9A0.283 (2)0.0472 (11)0.8852 (9)0.035*
H9B0.307 (2)0.1363 (10)0.9119 (9)0.035*
H9C0.378 (2)0.1079 (10)0.8360 (9)0.035*
C100.1541 (3)0.21341 (12)0.79847 (12)0.0451 (5)
H10A0.186 (2)0.2511 (12)0.8354 (10)0.045*
H10B0.237 (2)0.2126 (11)0.7604 (9)0.045*
H10C0.052 (2)0.2298 (11)0.7752 (9)0.045*
C110.16319 (19)0.06260 (9)0.84775 (8)0.0295 (4)
C120.3197 (2)0.10858 (12)0.84672 (11)0.0413 (4)
H12A0.409 (2)0.0726 (11)0.8373 (9)0.041*
H12B0.333 (2)0.1365 (11)0.8936 (10)0.041*
H12C0.312 (2)0.1483 (11)0.8092 (9)0.041*
C130.0240 (2)0.12139 (11)0.84791 (10)0.0368 (4)
H13A0.027 (2)0.1555 (10)0.8037 (9)0.037*
H13B0.029 (2)0.1577 (10)0.8913 (9)0.037*
H13C0.073 (2)0.0938 (11)0.8474 (8)0.037*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0243 (6)0.0224 (5)0.0297 (5)0.0022 (4)0.0025 (4)0.0020 (4)
O20.0261 (6)0.0472 (7)0.0303 (6)0.0026 (5)0.0022 (5)0.0071 (5)
O30.0292 (6)0.0370 (6)0.0273 (5)0.0035 (5)0.0049 (5)0.0028 (5)
C20.0270 (9)0.0261 (8)0.0277 (8)0.0022 (6)0.0017 (6)0.0056 (7)
C30.0276 (9)0.0351 (9)0.0343 (9)0.0010 (7)0.0036 (7)0.0039 (7)
C40.0336 (10)0.0432 (10)0.0370 (9)0.0037 (8)0.0111 (8)0.0037 (8)
C50.0402 (11)0.0325 (9)0.0429 (10)0.0081 (8)0.0085 (8)0.0067 (8)
C60.0356 (10)0.0237 (9)0.0365 (9)0.0020 (7)0.0015 (7)0.0013 (7)
C70.0262 (8)0.0214 (8)0.0284 (8)0.0036 (6)0.0007 (7)0.0025 (6)
C80.0261 (9)0.0314 (8)0.0298 (8)0.0001 (7)0.0000 (6)0.0021 (7)
C90.0255 (9)0.0433 (11)0.0376 (10)0.0003 (8)0.0025 (7)0.0068 (8)
C100.0416 (12)0.0424 (11)0.0515 (11)0.0029 (9)0.0118 (9)0.0111 (9)
C110.0328 (9)0.0273 (8)0.0284 (8)0.0019 (7)0.0047 (7)0.0038 (6)
C120.0433 (11)0.0372 (10)0.0434 (10)0.0118 (9)0.0052 (9)0.0008 (9)
C130.0450 (11)0.0290 (9)0.0365 (10)0.0052 (8)0.0051 (8)0.0043 (8)
Geometric parameters (Å, º) top
C7—O11.4368 (17)C6—H6B0.978 (17)
C2—O11.4382 (18)C7—C81.536 (2)
O2—C81.4399 (18)C7—H71.002 (16)
O2—H2O0.819 (18)C8—C91.518 (2)
O3—C111.4400 (18)C8—C101.530 (2)
O3—H3O0.824 (18)C9—H9A0.965 (18)
C2—C31.523 (2)C9—H9B0.973 (17)
C2—C111.542 (2)C9—H9C0.982 (17)
C2—H20.974 (16)C10—H10A0.963 (19)
C3—C41.530 (2)C10—H10B0.990 (19)
C3—H3A0.995 (16)C10—H10C1.000 (19)
C3—H3B0.958 (17)C11—C121.522 (2)
C4—C51.528 (3)C11—C131.523 (2)
C4—H4A1.006 (17)C12—H12A0.972 (19)
C4—H4B0.982 (18)C12—H12B0.986 (18)
C5—C61.523 (2)C12—H12C0.956 (18)
C5—H5A0.997 (18)C13—H13A0.992 (17)
C5—H5B1.004 (18)C13—H13B1.001 (17)
C6—C71.520 (2)C13—H13C0.938 (18)
C6—H6A0.961 (17)
C7—O1—C2119.40 (11)C8—C7—H7105.2 (8)
C8—O2—H2O112.4 (12)O2—C8—C9110.73 (13)
C11—O3—H3O110.0 (11)O2—C8—C10106.86 (14)
O1—C2—C3113.24 (12)C9—C8—C10110.82 (15)
O1—C2—C11109.35 (12)O2—C8—C7103.95 (12)
C3—C2—C11116.16 (13)C9—C8—C7112.94 (13)
O1—C2—H2103.2 (9)C10—C8—C7111.16 (14)
C3—C2—H2106.9 (9)C8—C9—H9A111.7 (10)
C11—C2—H2107.0 (9)C8—C9—H9B111.7 (10)
C2—C3—C4113.03 (14)H9A—C9—H9B107.3 (13)
C2—C3—H3A111.2 (9)C8—C9—H9C108.9 (10)
C4—C3—H3A110.5 (9)H9A—C9—H9C107.6 (14)
C2—C3—H3B107.3 (10)H9B—C9—H9C109.5 (14)
C4—C3—H3B107.7 (10)C8—C10—H10A110.5 (11)
H3A—C3—H3B106.7 (13)C8—C10—H10B108.7 (10)
C5—C4—C3114.74 (14)H10A—C10—H10B108.3 (15)
C5—C4—H4A109.9 (10)C8—C10—H10C109.5 (11)
C3—C4—H4A109.3 (10)H10A—C10—H10C112.0 (15)
C5—C4—H4B107.3 (10)H10B—C10—H10C107.7 (14)
C3—C4—H4B107.7 (10)O3—C11—C12106.22 (13)
H4A—C4—H4B107.6 (13)O3—C11—C13107.98 (13)
C6—C5—C4115.89 (15)C12—C11—C13110.66 (15)
C6—C5—H5A108.1 (10)O3—C11—C2110.18 (12)
C4—C5—H5A108.4 (10)C12—C11—C2111.54 (14)
C6—C5—H5B108.8 (10)C13—C11—C2110.12 (13)
C4—C5—H5B108.9 (9)C11—C12—H12A111.6 (11)
H5A—C5—H5B106.2 (13)C11—C12—H12B108.6 (10)
C7—C6—C5112.79 (14)H12A—C12—H12B110.7 (14)
C7—C6—H6A110.7 (9)C11—C12—H12C106.9 (11)
C5—C6—H6A108.9 (10)H12A—C12—H12C109.8 (14)
C7—C6—H6B108.7 (9)H12B—C12—H12C109.0 (14)
C5—C6—H6B110.0 (10)C11—C13—H13A109.8 (10)
H6A—C6—H6B105.6 (13)C11—C13—H13B110.6 (10)
O1—C7—C6108.51 (12)H13A—C13—H13B108.7 (13)
O1—C7—C8106.62 (12)C11—C13—H13C111.5 (11)
C6—C7—C8116.56 (13)H13A—C13—H13C106.8 (14)
O1—C7—H7110.6 (9)H13B—C13—H13C109.4 (14)
C6—C7—H7109.3 (9)
C7—O1—C2—C335.73 (17)C6—C7—C8—O2168.50 (13)
C7—O1—C2—C1195.51 (14)O1—C7—C8—C949.88 (17)
O1—C2—C3—C447.03 (18)C6—C7—C8—C971.42 (18)
C11—C2—C3—C4174.81 (13)O1—C7—C8—C10175.18 (13)
C2—C3—C4—C585.78 (19)C6—C7—C8—C1053.88 (19)
C3—C4—C5—C664.5 (2)O1—C2—C11—O358.09 (16)
C4—C5—C6—C752.3 (2)C3—C2—C11—O371.58 (17)
C2—O1—C7—C695.30 (14)O1—C2—C11—C12175.81 (13)
C2—O1—C7—C8138.41 (12)C3—C2—C11—C1246.14 (19)
C5—C6—C7—O177.03 (17)O1—C2—C11—C1360.91 (16)
C5—C6—C7—C8162.67 (14)C3—C2—C11—C13169.41 (14)
O1—C7—C8—O270.20 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2O···O3i0.819 (18)1.859 (18)2.6705 (16)170.7 (17)
O3—H3O···O20.824 (18)1.873 (18)2.6921 (17)172.4 (17)
Symmetry code: (i) x1/2, y, z+3/2.

Experimental details

Crystal data
Chemical formulaC12H24O3
Mr216.31
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)173
a, b, c (Å)8.4400 (16), 16.473 (3), 18.470 (5)
V3)2567.9 (10)
Z8
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.25 × 0.20 × 0.10
Data collection
DiffractometerBruker-Nonius KappaCCD
Absorption correctionMulti-scan
(SADABS; Bruker–Nonius, 2002)
Tmin, Tmax0.978, 0.988
No. of measured, independent and
observed [I > 2σ(I)] reflections
20554, 2926, 1811
Rint0.082
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.102, 1.02
No. of reflections2926
No. of parameters208
H-atom treatmentOnly H-atom coordinates refined
Δρmax, Δρmin (e Å3)0.24, 0.17

Computer programs: COLLECT (Nonius, 1999), DIRAX/LSQ (Duisenberg et al., 2000), EVALCCD (Duisenberg et al., 2003), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected bond angles (º) top
O1—C7—C6108.51 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2O···O3i0.819 (18)1.859 (18)2.6705 (16)170.7 (17)
O3—H3O···O20.824 (18)1.873 (18)2.6921 (17)172.4 (17)
Symmetry code: (i) x1/2, y, z+3/2.
 

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